Coenzyme A (CED0000998)

Record Information
Version1.0
Creation Date2016-05-26 05:35:04 UTC
Update Date2026-05-14 17:23:50 UTC
Accession NumberCHEM035215
Identification
Common NameCoenzyme A
ClassSmall Molecule
Description
Coenzyme A is a compound with the chemical formula C21H36N7O16P3S. Coenzyme A belongs to the purine ribonucleotides, a subclass of purine nucleotides within the organic compounds. With an average molecular weight of 767.53 g/mol, Coenzyme A is a heavy molecule. In industrial applications, this substance is utilized as a softener and conditioner. It has been identified in three recorded sources, specifically within building and construction materials such as ladders, as well as electrical and electronic equipment including antennas and amplifiers. Coenzyme A interacts with 42 recorded protein targets. These include the Fatty acid metabolism regulator protein (fadR), Histone acetyltransferase KAT5, and the enzyme 3-hydroxy-3-methylglutaryl-coenzyme A reductase (HMGCR). Additionally, it acts as an inhibitor of Galactoside O-acetyltransferase (lacA). The compound also interacts with 38 other proteins.
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3'-Phosphoadenosine-(5')diphospho(4')pantatheineChEBI
[(2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydrofuran-2-yl]methyl (3R)-3-hydroxy-4-({3-oxo-3-[(2-sulfanylethyl)amino]propyl}amino)-2,2-dimethyl-4-oxobutyl dihydrogen diphosphateChEBI
CoAChEBI
CoA-SHChEBI
CoASHChEBI
Coenzym aChEBI
HSCoAChEBI
Koenzym aChEBI
[(2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydrofuran-2-yl]methyl (3R)-3-hydroxy-4-({3-oxo-3-[(2-sulfanylethyl)amino]propyl}amino)-2,2-dimethyl-4-oxobutyl dihydrogen diphosphoric acidGenerator
[(2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydrofuran-2-yl]methyl (3R)-3-hydroxy-4-({3-oxo-3-[(2-sulphanylethyl)amino]propyl}amino)-2,2-dimethyl-4-oxobutyl dihydrogen diphosphateGenerator
[(2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydrofuran-2-yl]methyl (3R)-3-hydroxy-4-({3-oxo-3-[(2-sulphanylethyl)amino]propyl}amino)-2,2-dimethyl-4-oxobutyl dihydrogen diphosphoric acidGenerator
a, CoenzymeHMDB
18-CoA-18-oxo-Dinor-LTB4HMDB
Acetoacetyl coenzyme A sodium saltHMDB
CoA HydrateHMDB
coenzyme A HydrateHMDB
coenzyme A-SHHMDB
coenzyme ASHHMDB
Depot-zeelHMDB
Propionyl CoAHMDB
Propionyl coenzyme AHMDB
S-PropanoateHMDB
S-Propanoate CoAHMDB
S-Propanoate coenzyme AHMDB
S-Propanoic acidHMDB
S-Propionate CoAHMDB
S-Propionate coenzyme AHMDB
ZeelHMDB
Coenzyme AHMDB
Chemical FormulaC21H36N7O16P3S
Average Molecular Mass767.534 g/mol
Monoisotopic Mass767.115 g/mol
CAS Registry Number85-61-0
IUPAC Name{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-2,2-dimethyl-3-({2-[(2-sulfanylethyl)carbamoyl]ethyl}carbamoyl)propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
Traditional Namecoenzyme A
SMILESCC(C)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N)C(O)C(=O)NCCC(=O)NCCS
InChI IdentifierInChI=1S/C21H36N7O16P3S/c1-21(2,16(31)19(32)24-4-3-12(29)23-5-6-48)8-41-47(38,39)44-46(36,37)40-7-11-15(43-45(33,34)35)14(30)20(42-11)28-10-27-13-17(22)25-9-26-18(13)28/h9-11,14-16,20,30-31,48H,3-8H2,1-2H3,(H,23,29)(H,24,32)(H,36,37)(H,38,39)(H2,22,25,26)(H2,33,34,35)/t11-,14-,15-,16?,20-/m1/s1
InChI KeyRGJOEKWQDUBAIZ-DRCCLKDXSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as coenzyme a and derivatives. These are derivative of vitamin B5 containing a 4'-phosphopantetheine moiety attached to a diphospho-adenosine.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleotides
Sub ClassPurine ribonucleotides
Direct ParentCoenzyme A and derivatives
Alternative Parents
Substituents
  • Coenzyme a or derivatives
  • Purine ribonucleoside diphosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Ribonucleoside 3'-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • Organic pyrophosphate
  • Pentose monosaccharide
  • Monosaccharide phosphate
  • 6-aminopurine
  • Purine
  • Imidazopyrimidine
  • Aminopyrimidine
  • Monoalkyl phosphate
  • Organic phosphoric acid derivative
  • N-substituted imidazole
  • Phosphoric acid ester
  • Monosaccharide
  • Alkyl phosphate
  • Pyrimidine
  • Imidolactam
  • Imidazole
  • Azole
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Secondary alcohol
  • Oxacycle
  • Alkylthiol
  • Azacycle
  • Organoheterocyclic compound
  • Carboximidic acid
  • Carboximidic acid derivative
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organooxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic oxide
  • Primary amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Organosulfur compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility4.64 g/LALOGPS
logP-0.61ALOGPS
logP-5.7ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)0.82ChemAxon
pKa (Strongest Basic)4.01ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area346.56 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity162.74 m³·mol⁻¹ChemAxon
Polarizability68.21 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0002-9423572000-e15b71f4fd7a2baa5a35Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0000000900-7edeffc9e7f47049c6afNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0090200000-1bf2c11b25a8c3f528a7Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0490000000-b4270769e635660752ddNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-002s-5900000100-c920e6430f49f066a644Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-002r-6910000000-4dcac54e50dd5309af5cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-002r-8900000000-c9fc1dcc0fa2fecbf2f0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-6910232700-7e01b474d15249f13f3eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-2900200000-23c6af6438be416c3b4eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-057i-6900100000-a9a1d2f2162117f6ad81Not AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, H2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, H2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
6759.0Log mg/kg[3800:12000]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
498LaddersBuilding & ConstructionNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
1,4-dihydroxy-2-naphthoyl-CoA synthase structureClick to view 3D structure1,4-dihydroxy-2-naphthoyl-CoA synthaseP9WNP5Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)Predicted (SEA)0.0778492
Click to view 3D structureAminoglycoside acetyltransferaseQ70E71Enterococcus duransPredicted (SEA)0.0778492
N-alpha-acetyltransferase 40 structureClick to view 3D structureN-alpha-acetyltransferase 40Q86UY6HumansPredicted (SEA)0.233548
P2Y purinoceptor 1 structureClick to view 3D structureP2Y purinoceptor 1P47900HumansPredicted (SEA)4.43741
P2X purinoceptor 1 structureClick to view 3D structureP2X purinoceptor 1P51575HumansPredicted (SEA)1.63483
Click to view 3D structureHeat shock cognate 71 kDa proteinP19120Bos taurusPredicted (SEA)1.71268
Click to view 3D structureSensor protein kinase WalKQ9RDT3Staphylococcus aureusPredicted (SEA)1.71268
P2X purinoceptor 3 structureClick to view 3D structureP2X purinoceptor 3P56373HumansPredicted (SEA)1.86838
Click to view 3D structureP2Y purinoceptor 2P41231HumansPredicted (SEA)5.68299
Click to view 3D structureP2Y purinoceptor 1P49652Meleagris gallopavoPredicted (SEA)2.72472
ADP-ribose glycohydrolase MACROD1 structureClick to view 3D structureADP-ribose glycohydrolase MACROD1Q9BQ69HumansPredicted (SEA)1.86838
ADP-ribose glycohydrolase MACROD2 structureClick to view 3D structureADP-ribose glycohydrolase MACROD2A1Z1Q3HumansPredicted (SEA)1.86838
Click to view 3D structureS-adenosylmethionine synthase isoform type-2P18298Rattus norvegicusPredicted (SEA)1.40129
Click to view 3D structureP2Y purinoceptor 12Q9EPX4Rattus norvegicusPredicted (SEA)1.71268
Click to view 3D structureGTP:AMP phosphotransferase AK3, mitochondrialP29411Rattus norvegicusPredicted (SEA)1.71268
Click to view 3D structureP2Y purinoceptor 11Q96G91HumansPredicted (SEA)2.33548
P2X purinoceptor 4 structureClick to view 3D structureP2X purinoceptor 4Q99571HumansPredicted (SEA)1.40129
Click to view 3D structureP2Y purinoceptor 1P49651Rattus norvegicusPredicted (SEA)2.17978
Click to view 3D structureGlutamine--tRNA ligaseP00962Escherichia coli (strain K12)Predicted (SEA)1.55698
Click to view 3D structureGlycylpeptide N-tetradecanoyltransferaseP14743Saccharomyces cerevisiae S288cPredicted (SEA)0.0778492
Click to view 3D structure6-phosphogluconate dehydrogenase, decarboxylatingP85968Rattus norvegicusPredicted (SEA)0.778492
Click to view 3D structureAdenylate kinase 2, mitochondrialP29410Rattus norvegicusPredicted (SEA)1.79053
Click to view 3D structureGlutamate dehydrogenase 1, mitochondrialP00366Bos taurusPredicted (SEA)1.24559
Ribonuclease pancreatic structureClick to view 3D structureRibonuclease pancreaticP07998HumansPredicted (SEA)1.55698
Non-secretory ribonuclease structureClick to view 3D structureNon-secretory ribonucleaseP10153HumansPredicted (SEA)1.55698
Concentrations
Not Available
External Links
DrugBank IDDB01992
HMDB IDHMDB0001423
FooDB IDFDB022614
Phenol Explorer IDNot Available
KNApSAcK IDC00007258
BiGG IDNot Available
BioCyc IDCO-A
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCoenzyme_A
Chemspider ID79067
ChEBI ID15346
PubChem Compound ID87642
Kegg Compound IDC00010
YMDB IDYMDB00045
ECMDB IDECMDB01423
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Yano S, Li L, Le TP, Moseley K, Guedalia A, Lee J, Gonzalez I, Boles RG: Infantile mitochondrial DNA depletion syndrome associated with methylmalonic aciduria and 3-methylcrotonyl-CoA and propionyl-CoA carboxylase deficiencies in two unrelated patients: a new phenotype of mtDNA depletion syndrome. J Inherit Metab Dis. 2003;26(5):481-8.
2. Roe CR, Sweetman L, Roe DS, David F, Brunengraber H: Treatment of cardiomyopathy and rhabdomyolysis in long-chain fat oxidation disorders using an anaplerotic odd-chain triglyceride. J Clin Invest. 2002 Jul;110(2):259-69.
3. Kretschmer RE, Bachmann C: Methylcitric acid determination in amniotic fluid by electron-impact mass fragmentography. J Clin Chem Clin Biochem. 1988 May;26(5):345-8.
4. Osmundsen H, Bremer J, Pedersen JI: Metabolic aspects of peroxisomal beta-oxidation. Biochim Biophys Acta. 1991 Sep 11;1085(2):141-58.
5. Reihner E, Angelin B, Rudling M, Ewerth S, Bjorkhem I, Einarsson K: Regulation of hepatic cholesterol metabolism in humans: stimulatory effects of cholestyramine on HMG-CoA reductase activity and low density lipoprotein receptor expression in gallstone patients. J Lipid Res. 1990 Dec;31(12):2219-26.
6. Bergstrom T, Greter J, Levin AH, Steen G, Tryding N, Wass U: Propionyl-CoA carboxylase deficiency: case report, effect of low-protein diet and identification of 3-oxo-2-methylvaleric acid 3-hydroxy-2-methylvaleric acid, and maleic acid in urine. Scand J Clin Lab Invest. 1981 Apr;41(2):117-26.
7. Salen G, Batta AK, Tint GS, Shefer S: Comparative effects of lovastatin and chenodeoxycholic acid on plasma cholestanol levels and abnormal bile acid metabolism in cerebrotendinous xanthomatosis. Metabolism. 1994 Aug;43(8):1018-22.
8. Lehnert W, Junker A: [2-Methyl-3-oxovaleric acid: a characteristic metabolite in propionic acidemia]. Clin Chim Acta. 1980 May 21;104(1):47-51.
9. Wendel U, Zass R, Leupold D: Contribution of odd-numbered fatty acid oxidation to propionate production in neonates with methylmalonic and propionic acidaemias. Eur J Pediatr. 1993 Dec;152(12):1021-3.
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=11923312
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=13025483
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=15014152
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=15893380
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=18407920
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=19666462
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=20351285
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=2981478
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=7310833